Style Help: Cold Weather Business Casual

Several people have asked for business causal looks for cold weather, and whenever that happens I chuckle.  I live in sunny San Diego where “cold” for us is 60 degrees.  While I’m not totally foreign to cooler weather (thanks to growing up in Northern California and to traveling to the midwest and east coast for work trips) I still don’t feel adequate to talk about cold weather outfits.  Especially when some of you say you’re in -30 degrees!
That said, how about we make this a communal collection of tips instead?  I have a few to get us started, but I know some of you have magical cold weather tips up your sleeves that will really help others.  Please share them in the comments!
Today is specifically about business casual looks.  What counts as “business causal” can be a rather broad spectrum in terms of casual vs. business, so I tried to draw out general tips and outfit “formulas” that can be adapted to your own personal style or work environment needs.  The “formulas” are the basic skeletons of each outfit so if your style isn’t like mine you can still use the bare bones formula with pieces from your closet that suit your tastes and needs better.
NOTE: Assume I would add a coat and/or scarf to each of these outfits when necessary.

Blazer: Target (similar)  |  Sweater: Forever 21 (similar)  |  Top: (similar)  |  Pants: Old Navy (exact) |  Shoes: H&M (exact)  |  Bag: Nordstrom (exact)

Outfit #1:  Patterned button up + Pullover sweater + Blazer + Khakis or dress pants
The little pop of pattern underneath the sweater helps makes an otherwise all solid outfit slightly more interesting.  I usually add a short necklace when wearing a collared button up + pullover to add some femininity.

Tip #1:  Layer–yes, to stay warm, but also to stay COOL!  In some buildings the heat is cranked up, so even if it’s frigid outside you might be sweating indoors.  If that’s the case, you can peel off or add back layers as the heater fluctuates.  In the outfit above, the blazer could come off and the outfit would still be business casual appropriate.

Tip #2:  Thin layer underneath.  I wear a cami under almost every top, but in the winter I wear long sleeve heattechs from UNIQLO.  They’re really thin, soft, and stretchy, making a great layer.  I usually wear S/M and get these in M so it’s not too tight.  They come in various necklines and sleeve lengths.

Dress: LOFT  |  Cardigan: H&M  |  Tights: c/o White Plum (exact)  |  Boots: Target (similar)

Outfit #2:  Dress + Cardigan + Fleece lined tights + Boots
I actually like dresses more when it’s colder because it’s provides an extra layer over your legs whereas pants only have one layer.  If I wore a dress in a colder building I would go for a thicker dress, perhaps a thicker cardigan, add a scarf, and would definitely wear a layer of Heattech underneath.  (Plus the usual coat, gloves, etc.)

Tip #3:  Fleece lined tights.  Definitely a MUST HAVE.  Tights or leggings, it doesn’t matter, except that it’s harder to wear booties with leggings vs. tights.  Before I discovered these, I just sucked it up and let my legs be cold for the sake of not wanting to neglect my dresses and skirts all winter.  One option HERE.

Shirt: Old Navy (exact)  |  Sweater: Everlane (exact)  |  Skirt: Forever 21  |  Tights: Bare Necessities  |  Boots: Kohl’s

Outfit #3:  Button up + Pullover + Skirt + Fleece lined tights
Same top half layering as Outfit #1, just paired with a skirt.  I like this one because both the top and bottom halves have multiple layers.

Tip #4: Change shoes for commuting
I’ve never actually had to do this, but I’ve heard others talk about it.  Boots of some sort for commuting (rain, snow, or riding boots, depending on weather), then switching shoes once in the heated indoors.  I’ve read about these Hunter Tour boots that fold down for easy packing!

There are cheaper options besides Hunters (not foldable, though): this classic pair in 4 colorsa cute polka dot pair, a classic matte pair of Joules from Nordstrom or Target (diff colors), a striped pair, or lastly, a pretty quilted pair.


Sweater: Target (similar)  |  Blazer: H&M (similar)  |  Pants: Target (similar) |  Shoes: H&M (exact)  |  Bag: Target (exact)

Outfit #4: Patterned sweater + Blazer + Colored bottoms
Your sweater could be a turtleneck or you could add a white button up underneath for extra warmth.  Whatever the sweater is, pairing it with a blazer is a nice way to instantly look a little more polished while also giving you another layer.

Though some business casual settings allow jeans, I would have gone for maroon slacks instead if I had them.  Anyway, since the top was all neutrals I added colored bottoms, but it would work well with neutral bottoms too.

Tip #5: The right boots for straight-legged pants and slacks
Some people have asked how to wear boots with pants with non-skinny silhouettes.  It’s a great look for business casual–you just need the right kind of boots.  I personally haven’t managed to look put together with straight legged pants over riding boots, and instead I’d opt for a boot with a sleeker toe and at least a small heel to elongate the leg line.  (A boot like this, for example, or a knee-high version of that to stay warmer under slacks.)  These will look sleek with skirts and dresses too.

Unfortunately I don’t have any outfit examples of this because I don’t own boots like these anymore!

(Random fact: I used to wear straight legged jeans or slacks or dresses with boots like these all the time pre-blogging, even though I was much younger, in college, and didn’t need to dress polished in any way, shape, or form.  Totally did not fit my lifestyle or the environment I was in.  You could say it’s better to be overdressed than underdressed, but really it was so out of place that I just felt awkward!)

Alright, your turn!  What are some of your favorite tips for cold weather business casual dressing?  Favorite materials, pieces you think others would benefit from, layering secrets, etc.

OR, what cold weather business casual style problems do you need troubleshooted?

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  • Reply
    December 30, 2014 at 2:18 pm

    I really like the colour pallet for these outfits! I would wear every single outfit. Though it is hard for me to imagine it right now as I'm sitting with a fan pointed directly at me!

  • Reply
    KateAdam Florken
    December 30, 2014 at 2:25 pm

    It doesn't get 30 below in Arkansas by any means, but it does get pretty cold. I like a lot of these tips but honestly, in the winter, I don't wear anything BUT boots. I love the look of a pump like you have here, but for me, that just isn't possible when it's 28 degrees outside. So it's boots every single day.

    I am an attorney and so I often have to wear suits to the office when client matters come up. While suits may be nice, they aren't often very thick so I usually wear fleece-lined leggings underneath my suit pants. Our office is chilly — even with the heat turned up — so the leggings under the suit keeps me quite toasty.

    I do need to get better though with variety of my outfits. The last several weeks I've been throwing on long pants, black boots, and a sweater every single day and calling it. I think buying more button up shirts for layering and thinking about dresses and skirts over tights is a great way for me to start mixing it up.

    Thanks for the tips.


  • Reply
    Paula Spruell
    December 30, 2014 at 2:41 pm

    You did a great job with this! I live in Colorado, where it is currently 1 degree (that's not the norm…). Layers are key, thin layers so you don't look roly poly. I love cashmere for its soft, light warmth. Super cute outfits and inspiration!

  • Reply
    December 30, 2014 at 3:03 pm

    Addendum to tip #3 (or an additional tip in general): silk long johns (similar to your undertees from uniqlo)! Get them tightfitting since they'll be worn under everything. When it's REALLY cold (I live in MI) and I still want to wear a dress or skirt, I layer silk long johns underneath my fleece tights for an additional warm layer (which doesn't show through). The silk means that when I'm inside I won't get too hot, even though I'm wearing 2 layers on my legs. They're also great under pants if your dress slacks are thinner or lighterweight.

    Here's a link to an example of what I'm talking about:

  • Reply
    December 30, 2014 at 3:28 pm

    Oh to live in a land where 60 degrees is considered cold! Alas, I live in Minnesota and while he have had cold weather and snow since November we are quickly approaching our frigid temps very quickly (Jan., Feb., March). I have a pair of Cuddle-duds that are lightweight and very cozy. I wear the shirt more than I wear the pants… they are both very easy to wear. A lot of times I wear tights under my dress pants, because trouser socks/ nylon socks are not very warm. It keeps my feet from getting cold in my dress shoes and provides an extra layer on my legs without being cumbersome. I live in scarves during the winter! There are so many different ways to tie them and different weights so they are appropriate in pretty much every setting… At my job, business casual allows for puffer vests.. so it is not uncommon for me to be wearing tights, black dress pants, cuddle-duds t-shirt, black t-shirt, vest, and scarf with some sort of fun earrings. When the snow starts getting really deep or it is really cold I wear my Sorrel snow boots and change into my work shoes in the parking lot.

  • Reply
    December 30, 2014 at 3:47 pm

    I would say the biggest key for winter weather dressing is layers (duh). Instead of a skirt and sandals, it's now a skirt, plus tights (I find I don't like the look of fleece tights — any brand tips for ones that look less sweatery and more like tights?), plus warm socks plus riding boots. Instead of a summery top, it's now a cami +/- button-up, +/- sweater, +/- blazer +/- scarf. And that's how I survive winter in Vermont.

  • Reply
    Shopping My Closet
    December 30, 2014 at 4:16 pm

    I love looks #1 and 4!

    Liz @

  • Reply
    Erin @ Her Heartland Soul
    December 30, 2014 at 4:18 pm

    All such cute looks! I wish my cold weather was 60 degrees. With wind chill it's -17 degrees in Omaha right now.

    Her Heartland Soul

  • Reply
    December 30, 2014 at 5:38 pm

    SmartWool brand tends to look a little less sweatery than others. They're really warm too!

  • Reply
    December 30, 2014 at 6:05 pm

    Thanks for the suggestion!

  • Reply
    Lara Gephart
    December 30, 2014 at 8:01 pm

    Even though it hasn't gotten too terribly cold here in Central Illinois this year (minus one awful week in November), I have already busted out all my warm under clothes. I am mastering the "un-noticeable" layering in the winter so I don't look like the Michelin Man! My favorite thing to do is wear either the UNIQLO heattech or cuddle-dud shirts under my tops and then either cuddle-duds or fleece-lined leggings under my pants. If I'm wearing a dress, I always wear tall boots with tall socks and the fuzzy socks that I'm pretty sure are supposed to be house slippers on top. If I get too hot at work, I just slip the fuzzy socks off. I also have a pair of flats that I leave in my office so I can wear warm (less attractive) shoes outside and then change once I'm out of the elements.

    I also keep a fleece-lined jacket from UNIQLO (PS – LOVE that place! I wish we had an actual store here.) in my office at all times for the moments when wind is really blowing (I have huge windows in my office that are not sealed the best). It keeps me warm without feeling bulky.

    I think all the styles above can be easily adapted for the colder, below zero temps. The key is layering the ugly-but-warm-and-necessary items underneath and keeping the cute pieces on top!

  • Reply
    December 30, 2014 at 8:12 pm

    I wear leggings under almost every pair of pants all winter. About November – March. I have thin enough ones that I've never had a fitting problem and they really help with the warmth. And layers on top. I like at least 2 on every part of me before a coat.

  • Reply
    December 30, 2014 at 8:59 pm

    These are all really great ideas. As a blogger who lives in Chicago and writes primarily about business casual, I can attest to these all being wonderful suggestions. And much to my dismay, I have LOTS of experience getting dressed for work in cold weather – ugh!

    In addition to all the things you've shared, I've written a few posts recently that might be of some help as well regarding this issue.

    Tights are an awesome suggestion, especially the fleece ones you mentioned! Fleece is so popular right now so they're pretty easy to find at Target and other similar stores. I wrote a whole post on wearing colored tights to work here:

    I also recently wrote a post about how to "winterize" your work wardrobe and some tips I use to make just about anything in my closet work for work even in the coldest of weather. Hopefully some of these will be good tips. I walk to work, even when it's below zero, so I definitely have "commuting" shoes (which are heavy winter boots in the middle of the winter). 🙂 And I'm super jealous that you live in San Diego!

    Lastly, I wrote this post about tips for "dressing well in not-so-swell weather". It includes some outfits ideas as well as some of my tips based on lots of experience living in a climate where myriad weather often dictates what I wear to work.

    I hope you and your readers find these helpful in addition to your great tips! And as always, thanks for sharing all your great style insights. I always enjoy coming back to read what you're sharing!


  • Reply
    December 30, 2014 at 9:44 pm

    My main tip for warm dressing is sheepskin insoles, I put them in my tall boots and booties and instantly help with warming up without looking like you are going hiking in a blizzard, they are also great in wellies (rainboots) which tend to be quite cold to wear.

    I also do the changing at the office sometimes, I had to go to a course in Toronto in a snow storm one February and wore fleece pants over tights every day to and from the course, just carried a skirt in my purse and changed when I got there, I was fine in my knee high boots because of the sheepskin insoles.

    Additionally there are some natural fabrics that are a little more pricey but are much better insulators, I'm ok with poly blouses most of the year but in colder weather a 100% silk shirt will actually be warmer, same with mixed fabric sweaters and cardigans, in the winter I reach only for my 100% merino or cashmere tops.

    I keep an extra cardigan at my office in case I need to add a layer, there is always a gray pashmina over my chair that I can use as well.

    Worst comes to the worst if you have an outfit with pockets you can put some handwarmers in them to keep yourself warm- I am a huge fan of the zippo reusable one.

  • Reply
    Andréa Christine
    December 30, 2014 at 10:05 pm

    I just moved to Toronto (from Atlanta) and this is some pretty solid advice. I'll definitely need to invest in some sheepskin insoles really soon!

  • Reply
    Midwest Girl
    December 31, 2014 at 2:37 pm

    Love this! I live in the midwest. Today it is -7. WITHOUT windchill. 🙂 I struggle with what sock/nylon combo to wear with skinny/shorter jeans when I don't want to wear boots. They are not professional over the pants. I love your sock-less shoe posts but they often make me chuckle because I can only wear those a few month of the year. I also struggle with what shoes to wear with dresses or skirts that are not boots, because again, they often aren't too professional for a conservative government environment. I get sick of trouser pants!

  • Reply
    December 31, 2014 at 4:08 pm

    Love your tips although I can't go out without socks on this time of the year 🙂 I wear lots of layers, scarves, fleece tights and tall boots to stay warm. If I want to wear boots with non skinny pants I just wear an ankle boot under them. I prefer that look in the winter with my work pants because it keeps my feet warmer.

  • Reply
    December 31, 2014 at 4:21 pm

    Uniqlo heattech leggings. Every single day in the winter, under my work pants. Fleece-lined tights if I'm wearing a dress. I need to try some of the heattech tops as well! If there's snow or ice on the ground, I'll wear snow boots and change my shoes once I get to the office.That way, I can still get some use of my pumps in the winter!

  • Reply
    Blue Labels Boutique
    December 31, 2014 at 6:59 pm

    Love all of these looks!

  • Reply
    Beth Moffett
    January 3, 2015 at 6:15 pm

    I am a true Canadian living an hour away from Toronto. My dad is the king of dressing for winter with no one noticing and I have learned many of his tricks. The following is usually just laughed off but you wouldn't believe the difference it makes.
    My #1 tip for anyone in below 30F is to wear long johns (aka. thermal underwear). I wear long johns every day under my jeans in the winter. My legs almost never feel cold. I used to wear mens long johns and just role down the top. Now lots of companies make very fancy long johns for women that look like they could be leggings but are incredibly warm. Under Armour and other similar companies make expensive versions but I recently fell in love with Hottotties which are more affordable. Most days I forget I'm even wearing them until I take them off at night.
    Tip #2 is that socks are never an option: they are mandatory. When snow is involved, socks need to be worn. I often put black socks under my black flats and you can't even tell. I know some will wear their big clunky boots to work and then take their socks and boots of to wear flats in the office. I know that when I wear my winter boots, my feet usually sweat a little. When you take off your socks and put on flats, honestly, your feet are a little ripe. Please spare your officemates from that awkward conversation. I also tend to wear wool sucks if I know my socks won't be showing at all for extra warmth.
    These 2 tips go hand in hand because people often wear socks and long johns wrong. For optimal warmth, tuck your long johns into your socks to create an airtight barrier. It looks silly but once your pants are over top no one will ever know what's going on underneath and you will be toasty warm all day.

  • Reply
    J Pow
    January 4, 2015 at 12:34 am

    I live in Michigan where the temp is currently 30's with it hittino the teens next week. This is pretty much what I do, I also work in a business casual environment. Booties work great with jeans or pants, skinny leg or not. Most of my work pants are bootleg or wide leg.

  • Reply
    January 4, 2015 at 10:36 pm

    I have been known to wear tights or leggings underneath my pants for an added layer of warmth 🙂 I also really like wearing active/compression leggings in lieu of tights with dresses and skirts in the winter. It adds so much more warmth, without making you all sweaty when you're inside, like fleece-lined tights can sometimes do. Plus, then I will layer on a thick pair of boot socks and riding boots, so my legs and feet are nice and toasty. I also know that when my neck is warm, my whole body is much more warm as well, so I wear lots of scarves in the winter as well!

  • Reply
    Audrey @ Putting Me Together
    January 5, 2015 at 12:55 am

    Amen to the scarves. When my neck is warm it's the equivalent to me wearing a cardigan in terms of warmth. So if it's not too cold (most days in SD) a scarf will suffice without a cardigan, or if it's cold, a scarf is like a second cardi. But now when I wear Addie in a carrier, she takes the place of a scarf. Little heater!

  • Reply
    January 8, 2015 at 11:10 pm

    Oh my gosh, I bet Addie is a little furnace! My cousin had a baby in November and she just started wearing him in a wrap, and she said it's been great to keep her warm during the bitterly cold days we've been having in MN lately!

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